Pharmaceutical product



Patented Aug. 6, 1929.

UNITED STATES PATENT OFFICE.

HANS KAI-IL AND LUDWIG SCHT TTZ, F ELBERFELD, GERMANY, ASSIGNORS TO WIN-THROP CHEMICAL COMPANY, INC., 01 NEW YORK, N. Y.

PHARMACEUTICAL PRODUCT.

No Drawing. Application filed March 24, 1927, Serial No. 178131, and inGermany November 6, 1922.

The present invention relates to compounds of the general formula:

wherein X represents halogen, R an alkylene group and R and R eitheralkyl groups or hydrogen atoms. 'lhey-possess a physiologic cal eii'ectupon the uterus and upon the blood vessels causing their contraction.They are therefore valuable substitutes for sccale cornutiun. They formneutral salts with acids which retain the above defined valuableproperties and are soluble in water and can be used For subcutaneousinjections.

The new products are generally yellowish oils soluble in alcohol formingcrystallizing salts with acids.

In order to illustrate our new process more fully the following exampleis given, the parts being; by weight 6 parts of sodium are dissolved in60 parts of alcohol and parts of thiourea are added. Subsequently 36parts of diethylaniino-ethyl chloride are added The reaction begins atthe ordinary temperature and is accelerated by warming. The mixture ispoured into water, the oil which separates is dried and distilledf It isa thick oil having most probably the form 1nula:-

wherein X re )resents halo' en R an all; lene group and R and R eitheralkyl groups or hydrogen atoms.

2. The process which comprises treating thio urea withdiethylamino-ethyl chloride in the presence of: sodium ethylate.

3. As new products the compounds of the general formula wherein Rrepresents an alkylene group and R and R represent either alkyl groupsor hydrogen atoms, said compounds being generally oils, soluble inalcohol, forming salts with acids, and being valuable substitutes :forsecale cornutuin.

t. As a new product the herein described diethylaminoethyl thio-urea,having most probably the formula which is a thick oil, boiling at from140- 1 13 C. under a pressure of 10 mnr, its hydrochloride crystallizingfrom alcohol in the shape of white needles and being a valuablesubstitute for secale cornutuln.

In testimony whereof we have hereunto set our hands.

HANS HAHL. LUDWVIG SCH UTZ.

